Why My iCloud Email Stopped Working in Outlook for Mac

When your email program suddenly chokes, it’s probably a good idea to first find out if your email provider has updated any of its policies that require you to take action.

Yes, my iCloud emails abruptly stopped showing up in my Microsoft Outlook for Mac program a few days ago. For the record, it was on June 15. My iMac presented a message warning me that something was very wrong and that it might be my password or user ID. But as far as I knew, nothing had changed.

Boy, was I wrong…

June 15 Can be Hazardous to Your Emails
And if you think you don’t need to worry about this particular tech glitch because you don’t use Outlook for Mac for email, be forewarned that this story affects all of your third-party apps that require a password to get to your iCloud email, calendar and contacts.

I scoured the web for possible solutions.
Hours later, I stumbled across this little detail:
(Thanks to 9to5Mac and Lifewire)

As of June 15, 2017, Apple changed its security policies for non-Apple apps. Now, you need to create app-specific passwords through Apple’s enhanced security protocols of “2-step verification” (older system) or “2-factor verification” (newer system).

What this means is you can’t sign into your non-Apple apps using your iCloud password. You’ve got to create app-specific passwords through Apple.

This is not at all a new process. But if you’ve been avoiding Apple’s verification protocols, now you have no choice but to comply or get kicked out of Apple’s ecosystem.

Give a Dad a Chance!
No doubt, better security bolted onto your iCloud account is wicked important. But it would have been nice to know that this was coming.

But as it turns out, Apple sent an email to me on May 16 explaining the change.
I didn’t see that one apparently…

And then I missed the friendly reminder that went out two days before the deadline.
Mea culpa.

So how hard is it to set it all up?
Not at all.

In fact, it’s easy via the Apple ID page, which houses all of your account details and where you can create these à la carte passwords.

Father’s Day Gift from Apple
Look, I know I wasn’t paying attention. And I was given fair warning… twice.

But Apple… did you have to make the deadline right before Father’s Day?!
I mean… chances are there are other dads out there who ran afoul of this change.
I can’t be the only one.

And wouldn’t it be safe to assume we’ve all got other plans on Father’s Day weekend beyond having to spend time trying to figure out how to get our emails working again?

Choosing a different week would have been better.
(Just a pedestrian point of view from one of your faithful users out there in the trenches)

And to all of you ‘IT Guy’ dads out there who dodged this particular bullet, please hear me: If you don’t have the spare time to make your tech updates in a timely manner and hope to keep the status quo going for as long as possible… you can only wait for so long!

And then it catches up with you.
That’s the reality.
Happy Father’s Day.

Now put away your new tie and get to work.
(And read all of your Apple emails!)